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Details

Stereochemistry ACHIRAL
Molecular Formula C26H32N2O5
Molecular Weight 452.5427
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENSACULIN

SMILES

COC1=CC=CC=C1N2CCN(CCCOC3=CC4=C(OC(=O)C(C)=C4C)C=C3OC)CC2

InChI

InChIKey=FQELZLMTAPJJOL-UHFFFAOYSA-N
InChI=1S/C26H32N2O5/c1-18-19(2)26(29)33-23-17-24(31-4)25(16-20(18)23)32-15-7-10-27-11-13-28(14-12-27)21-8-5-6-9-22(21)30-3/h5-6,8-9,16-17H,7,10-15H2,1-4H3

HIDE SMILES / InChI
Molecular Formula C26H32N2O5
Molecular Weight 452.5427
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/18465518 | https://www.ncbi.nlm.nih.gov/pubmed/9590466

Ensaculin is related to naturally occurring benzopyranones like scoparone. The compound is a potent functional antagonist of excitatory amino acid-induced convulsions and mortality. In receptor-binding studies, Ensaculin showed high affinity to dopaminergic (D2, D3), serotoninergic (5-HT1A, 5-HT7), and adrenergic (A1a, A1b) receptors in the nanomolar range. Ensaculin antagonizes NMDA responses in a voltage-dependent manner. Various studies support the notion that this compound could indeed have a broad range of nootropic properties. Although few patients presented postural hypotension and dizziness after receiving ensaculin in phase I clinical trials, this drug candidate was further discontinued in phase III due to potential side effects.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 8.0 nM [IC50]
Antagonist
2778
 16.6 nM [IC50]
Antagonist
2778
 9.3 nM [IC50]
Binding Agent
1064
 27.7 nM [IC50]
Binding Agent
1064
 277.0 nM [IC50]
Binding Agent
1064
 4.7 nM [IC50]
Binding Agent
1064
 2.4 nM [IC50]
Antagonist
2778
 20.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
9.6 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
16.8 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
20 mg 1 times / day multiple, oral
dose: 20 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
35.6 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
25.4 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
7.6 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
43.8 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
99.5 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
20 mg 1 times / day multiple, oral
dose: 20 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
202.9 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
255 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
61.8 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.3 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
11.1 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
20 mg 1 times / day multiple, oral
dose: 20 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
13.7 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
16.1 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
17.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9590466
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENSACULIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Sourcing

Sourcing

Vendor/AggregatorIDURL
MuseChem
M091519
https://www.musechem.com/product/M091519.html
PubMed

PubMed

TitleDatePubMed
KA-672 Dr Wilmar Schwabe GmbH & Co.
1998 May
Ensaculin (KA-672 HCl): a multitransmitter approach to dementia treatment.
2002 Summer
Anseculin improves passive avoidance learning of aged mice.
2003 Mar
Patents

Patents

20040058896
57
DE 4111861
1
US5428038
1
WO 9218493
1

Sample Use Guides

In Vivo Use Guide
5 mg to 20 mg once daily.
Route of Administration: Oral
In Vitro Use Guide
Ensaculin inhibited rat brain acetylcholinesterase (AChE) activity in vitro with an IC50 of 0.36 uM without affecting the activity of butyrylcholinesterase or arylacylamidase.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:45:48 GMT 2023
Edited
by admin
on Sat Dec 16 17:45:48 GMT 2023
Record UNII
869PGR00AT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENSACULIN
INN  
INN  
Official Name English
7-METHOXY-6-(3-(4-(O-METHOXYPHENYL)-1-PIPERAZINYL)PROPOXY)-3,4-DIMETHYLCOUMARIN
Common Name English
ensaculin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C45597
Created by admin on Sat Dec 16 17:45:48 GMT 2023 , Edited by admin on Sat Dec 16 17:45:48 GMT 2023
Code System Code Type Description
PUBCHEM
208923
Created by admin on Sat Dec 16 17:45:48 GMT 2023 , Edited by admin on Sat Dec 16 17:45:48 GMT 2023
PRIMARY
NCI_THESAURUS
C74243
Created by admin on Sat Dec 16 17:45:48 GMT 2023 , Edited by admin on Sat Dec 16 17:45:48 GMT 2023
PRIMARY
FDA UNII
869PGR00AT
Created by admin on Sat Dec 16 17:45:48 GMT 2023 , Edited by admin on Sat Dec 16 17:45:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID10870034
Created by admin on Sat Dec 16 17:45:48 GMT 2023 , Edited by admin on Sat Dec 16 17:45:48 GMT 2023
PRIMARY
MESH
C112452
Created by admin on Sat Dec 16 17:45:48 GMT 2023 , Edited by admin on Sat Dec 16 17:45:48 GMT 2023
PRIMARY
SMS_ID
100000080240
Created by admin on Sat Dec 16 17:45:48 GMT 2023 , Edited by admin on Sat Dec 16 17:45:48 GMT 2023
PRIMARY
EVMPD
SUB06551MIG
Created by admin on Sat Dec 16 17:45:48 GMT 2023 , Edited by admin on Sat Dec 16 17:45:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL1963107
Created by admin on Sat Dec 16 17:45:48 GMT 2023 , Edited by admin on Sat Dec 16 17:45:48 GMT 2023
PRIMARY
INN
7339
Created by admin on Sat Dec 16 17:45:48 GMT 2023 , Edited by admin on Sat Dec 16 17:45:48 GMT 2023
PRIMARY
CAS
155773-59-4
Created by admin on Sat Dec 16 17:45:48 GMT 2023 , Edited by admin on Sat Dec 16 17:45:48 GMT 2023
PRIMARY
WIKIPEDIA
ENSACULIN
Created by admin on Sat Dec 16 17:45:48 GMT 2023 , Edited by admin on Sat Dec 16 17:45:48 GMT 2023
PRIMARY
Related Record Type Details
NMDA RECEPTOR
TARGET -> INHIBITOR
Related Record Type Details
Structure of ENSACULIN
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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